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Authors: Jeff Passan

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“What we're trying to do is condition him for the long haul to increase his volume and innings and also help him improve his command and the consistency of his pitches,” Duquette said. “We will monitor both the timing and workload and the amount and the rest, because we'd like him to build up to be a thirty-five-start-a-year pitcher who can be a workhorse.”

Bundy took five, six, seven, eight, sometimes nine days between starts. His heaviest workload over the season's first four months was eighty-four pitches. No evidence existed to suggest this was the proper way to treat a pitcher like Bundy. Baseball was testing pure hypotheses on its six-million-dollar man.

When he debuted in the major leagues that September as a teenager, Bundy looked every bit the superstar-in-waiting, throwing two scoreless innings of relief. Going into the spring of 2013, Bundy was a few minor league starts away from cracking the Orioles' rotation. Then he felt a pain in his arm. Rest didn't help. Rehab didn't work. In June, a little more than two years after Baltimore drafted him, Dylan Bundy underwent Tommy John surgery.

The elbow scares teams because no matter what they try, it breaks. Throw a lot of pitches and it breaks. Limit the pitches and it breaks. Implement a piggyback rotation like the Houston Astros, in which two “starting pitchers” throw back-to-back in the same game, and it breaks. The more teams learn, the more they try, the more frustration mounts because nothing is working. Perhaps solutions exist down the granular path Rany Jazayerli paved. It's not just about pitch count but pitches per inning. And it's not just about pitches per inning but the velocity of those pitches. And it's not just about velocity but the spin rate. And it's not just about the spin but how tired the arm was when spinning the ball. And not just how tired the arm was but how the rest of the body compensated for it, from head to toe and every little link of the kinetic chain in between.

We could build three hundred–inning pitchers again. I firmly believe this. With the advances in training, the improvements in nutrition, the knowledge passed along from Bennett and the Bonesetter to Jobe and Kerlan to Yocum and Andrews to ElAttrache and this generation of doctors, we could condition baseball players at every level to throw, throw, throw. Here's the catch: The upshot does not match the price. It would force baseball to acknowledge that many arms will break so a handful of survivors can reach what amounts to little more than an arbitrary round number. Baseball won't traffic in collateral damage, won't sacrifice the many for the one. It made that choice long ago, and it was the right one. Three hundred innings is not a sorely missed benchmark. It's a false idol.

Its pursuit left us with the desiccated arms of Mark Fidrych and Ernie Broglio and Steve Busby, and the sense is that the arm is less than it used to be. It leaves teams spitballing, glomming onto concepts like the one offered by
Sports Illustrated
writer Tom Verducci, who for years has suggested year-over-year inning increases of more than thirty are dangerous for young pitchers. Sabermetricians claim to refute his hypothesis annually, the legacy
of Craig Wright alive and well, though the conclusions ought to contain a caveat: pitching by its nature is dangerous on the arm.

The confusion filters down to Koufax, and he's not sure what to believe. He wants pitchers to throw more, but he sees the year-round throwing in which pitchers today partake, and he isn't certain his generation threw more over the course of twelve months than modern pitchers.

“People train all winter, this and that,” Koufax said. “Is that good? I don't know.”

The edges of Koufax's lips curled outward, his face puzzled, and he raised his left arm in a shrug. His moneymaker moves without pain, like Dr. Kerlan told him it would, and he never regretted the choice, not even during his two favorite times of year, spring training and the World Series. The wisdom he gained in a life away from baseball taught him that the arm is something neither he nor Dr. Kerlan nor any professed expert could fully comprehend, not until better diagnostic methods exist. There are things about it that we know, truisms proven over years.

It's the things we don't that make it so frightening.

T
HE ULTIMATE ENDGAME IS A
meeting. It is Scott Boras and some lawyers in suits, and reams of paper with numbers on them. It is Matt Harvey, one of baseball's best pitchers, the Dark Knight of Gotham, reduced to nothing more than a risk valuation.

“I sat with an insurance company for three and a half weeks to figure out an insurance policy for Matt Harvey,” Boras said. “What is the reason? His psychology. I'm not doing this because I think something's wrong with the player. I need psychology. I need a pillow so he sleeps well. I'm going to pay for it. And pay dearly.”

Even Boras, somebody who speaks in absolutes, won't do so about the arm. Ultimately, he believed the Mets handled Harvey in a proper fashion, and he still bought a policy in September 2015
that would pay out millions of dollars in case of an arm injury that affected Harvey's expected free agent contract or ended his career. Though it was macabre, like a baseball morbidity table, it was nothing new.

Over the last thirty-five years, Dan Burns saw baseball pitchers through the same prism: risky. He works at Pro Financial Services, a Chicago-based insurance company that specializes in coverage on pro athletes. (It did not handle Harvey's insurance contract.) Burns estimates he has written policies for thousands of pitchers. His job is to understand what he's insuring against, and nobody can tell him why pitchers are getting hurt. After the rash of Tommy John surgeries early in the 2010s, he hoped for change that never came. “It was not a blip on the radar,” Burns said. “I don't know how long this trend is going to continue. Nothing I've seen points to it stopping.”

So Burns writes up policies, and teams take them out on their highest-paid pitchers, and, in rare cases, someone like Matt Harvey pays a literal premium for the privilege of pitching past his innings limit. “[Insurance] does help your mind a little bit in the future,” Harvey said.

The financial future, whether through the policy or on the mound, is guaranteed. When the Detroit Tigers offered pitcher Max Scherzer a six-year, $144 million contract in 2014, he turned it down. Unknown at the time, Boras had spent the previous seven months negotiating a tax-free $40 million insurance payout for Scherzer in case of injury. The policy cost $750,000. The Washington Nationals gave Scherzer a seven-year, $210 million deal. His $750,000 bet paid $66 million.

Sandy Koufax was right. Baseball is about the money. Even if the sport can't figure out how to use pitchers correctly, it damn sure knows how to pay them.

CHAPTER 7
Pay the Man

A
T AROUND FOUR O'CLOCK IN
the morning on December 8, 2014, Theo Epstein was mildly buzzed, severely sleep deprived, and looking to shell out $155 million. During the previous month, he made a video, sent gifts, wrote letters, and basically used every last morsel of his famous charm to convince Jon Lester to take his money. Now, sitting in a high-floor suite at the Manchester Grand Hyatt in San Diego, his jeans stained with Jägermeister, his patience eroded to the rawest nerve, Epstein alternated between euphoria and delirium. If he couldn't spend his money before the sun rose, he was going to get into a fight.

Epstein is the prince of baseball. A decade ago, he was the boy-wonder general manager who piloted the Boston Red Sox to their first World Series championship in eighty-six years. Now he was the president of baseball operations for the only franchise more woebegone than Boston: the Chicago Cubs, who hadn't won a World Series since Teddy Roosevelt was in the White
House. Almost everybody in baseball likes Epstein and his disarming sense of humor, his eternal pragmatism, and his appeal to both the intuitive and the analytical sides of the game. He's the guy who could sit at lunch one day with the jocks, the next day with the nerds, and not only look comfortable in both places but own the table.

Among the few men in the business of baseball capable of wresting that power from Epstein, two were in the suite. Seth and Sam Levinson, a couple of Brooklyn-born and -bred brothers who ran the ACES agency, lived for nights like this. They played to every sibling stereotype. Seth was the older one, brandishing his law degree, always crunching numbers, in full command of a room whenever he walked through the door. Sam was his perfect complement, the ultimate schmoozer, as good with equipment vendors as he was with executives. He was the one who kept pouring the drinks.

Over the previous quarter century, the Levinsons had negotiated more than $1 billion in contracts for a coterie of All-Stars and MVPs they represented. Lester—thirty years old, left-handed, a paragon of durability, two hundred–inning seasons a given, his arm scar-free—had the biggest price tag of them all. He had clinched the 2007 World Series a year after a cancer diagnosis and was among baseball's five best pitchers in 2014. The Levinsons had spent the previous month leveraging teams and offers with an eye on baseball's annual Winter Meetings, where they would sequester themselves in their hotel room and let a historic deal come to them.

“They get you into their world, into their suite,” Epstein said. “It's two in the morning, three in the morning, and they just keep going. They wear you down, and it's almost like you start hallucinating and they become vampire-like guys who convince you that they're right.”

Epstein and his consigliere, Jed Hoyer, the Cubs' general manager, didn't usually spend the Winter Meetings boozing deep into
the night. On this night, they shared laughter over drinks slugged and spilled, the latter courtesy of an ACES agent named Peter Pedalino, who told a joke, delivered the punch line, and, in the midst of slapping Epstein on the back, proceeded to knock a red Solo cup of Jäger on his jeans. If grogginess and a dry-cleaning bill were the tax on the $155 million the Cubs were ready to drop, so be it.

Already Epstein and Hoyer surged past the $150 million ceiling they set at the start of the pursuit, certain it would get the Levinsons to say yes. It didn't. And that started to piss Epstein off. He wanted Jon Lester, wanted him despite algorithms that warned against such desires given the high rates of failure among the small sample of thirty-and-older players with long-term contracts and the truth about Lester's arm that neither the Cubs nor any other team knew.

Early in the free-agent process, Lester flew into Cincinnati to visit Timothy Kremchek, the doctor who had performed Todd Coffey's first Tommy John surgery. If any serious problems in Lester's arm existed, better to find out first and prevent a nightmare scenario in which he agreed to terms with a team, only for him to fail the physical and neuter his market. An MRI revealed slight fraying on Lester's rotator cuff, typical weathering on an arm used as much as his. The ultrasound on Lester's elbow confirmed the presence of something he long suspected lurked inside: a bone chip. The UCL itself looked fine, thankfully, and the range of motion Kremchek measured through manual testing was better than expected, but a little grenade floated near his ligament, and at some point it would warrant surgery.

For a week or so every spring, the chip bothered Lester, only for the pain to disappear as his arm worked into game shape. He didn't consider it an issue, and he figured teams wouldn't, either. Maybe that was naive. Maybe it was realistic. He wasn't going to reveal it until it was absolutely necessary, and with a deluge of teams interested in giving him nine figures, Lester played coy,
even as the Cubs tried to close a deal. Epstein thought the Levinsons were stalling, so he started to push, pester. Epstein's usually unflappable demeanor gradually became a sleep-deprived, emotional buzz saw. Sam Levinson stood up, engaged Epstein, and a screaming match erupted, about nothing and everything, about Lester and even Julio Lugo—really, Julio Lugo—a former Red Sox shortstop and ACES client Epstein had signed to a regrettable four-year, $36 million deal in 2006. They were two alphas at the top of their professions, adversaries only because the rules pitted them against each other. They said what needed to be said, and then Theo Epstein said, “Let's just fucking end this fucking thing,” and then Sam Levinson agreed, and the next day, after he shook off the cobwebs of the previous night, Levinson called Jon Lester and asked if he wanted to be a Chicago Cub for the next six years. Twenty-four hours later, a Major League Baseball team bet almost a sixth of a billion dollars on one arm.

N
O MATTER HOW MUCH I
learned during three years trying to understand the arm, it still stupefied me every time a team gave $100 million to a pitcher. Baseball is rich. Players must get a certain cut of revenues. Thus, pitchers get paid. It is a simple equation, simultaneously true and wildly unsatisfactory because of the arm's guiding principle: it probably will break. I needed to see how teams got to this juncture, how a player handled everything that came with it, both sides of the most inefficient market in professional sports: baseball free agency.

So on November 13, 2014, I called Jon Lester. He'd agreed to let me follow his free agency from the inside, to watch the process and understand what compels a team to lavish nine figures on a pitcher with nearly twenty thousand pitches on his odometer. I wondered about his arm, too, because even though he passed the age-thirty threshold with no problems, he would slide into an MRI tube before he put pen to paper on his contract, and it
would reveal just how much wear and tear a team is willing to tolerate. Between Lester and right-hander Max Scherzer, a pair of presumed $100 million-plus pitchers were hitting the market after the two most catastrophic years of arm injuries on record, an ugly streak after which then–commissioner Bud Selig and Major League Baseball vowed to figure out the arm. Teams aren't nearly as motivated to solve the mysteries of the arm once and for all as they are to go all-in on free agent hurlers and cross their fingers.

For his foray into free agency Lester had to thank Carmine, the computer program that helps shape the Boston Red Sox's decision making. Before the 2014 season, the Red Sox and Lester agreed to negotiate on a long-term contract extension. He wanted to re-sign, even if he had to give the team a hometown discount. Boston had drafted him, developed him, stuck with him as he beat non-Hodgkin's lymphoma, watched him get married and have kids. Even if he was most comfortable in a deer blind, camo'd like a soldier, bow or rifle in hand, Lester felt at home in Boston. Wanderlust wasn't his thing.

Then came the Red Sox's and Carmine's first offer: four years, $70 million. Opposing executives were mystified. Lester's teammates were horrified. The Red Sox vowed they would never give a pitcher in his thirties a six- or seven-year deal, and such prudence brought them rancor external and internal. It wasn't viewed as a lowball offer; it was a joke, the mighty Red Sox too stubborn to budge on a homegrown kid who embodied so many of the organization's values. Far inferior pitchers received far bigger contracts, and here were the Red Sox, taking Carmine's actual suggestion—$68 million over four years—and bumping it a whole 3 percent.

As much as Lester tried to rationalize the offer—every negotiation has a starting point—he couldn't explain it. He didn't want to hear that long-term deals for pitchers in their thirties are among the very worst investments a team can make. Lester rejected the offer, even if it felt like the absolute height of ingratitude to say no
to tens of millions of dollars. He grew up in Puyallup, Washington, a city of about forty thousand southeast of Tacoma. Lester's dad, John, was a cop and his mom, Kathie, drove asphalt trucks and snowplows. “You're talking about seventy million dollars,” Lester said. “Seventy million is a lot of money. And no matter how you talk about it, you sound like a typical athlete. It's not a slap in the face. It wasn't.

“It's not about the money,” he said. Lester stopped and snickered at his own cliché. Except he swore it would be true, even if the Major League Baseball Players Association depended on players like Lester to set new salary thresholds. “I'll know where I'm going,” he said, “when it feels right.”

He wanted what was best for his family, especially following an ugly incident in Oakland, where he landed in a July 2014 trade after Boston's bungled first offer and failed attempts at further negotiations. The wife of an A's player was assaulted at a home game, and it scared Lester and his wife, Farrah, who knew only the relative safety of Fenway Park for them and their two sons, Hudson and Walker. Lester wanted a team that would prioritize his charitable work, too, especially his NVRQT campaign that raised money to combat childhood cancer. And he wanted to win, his two gold World Series rings anxious to be joined by a third.

“There's a happy medium,” Lester said. “What people need to understand, too, is if you're talking 120 and 140, in the greater scheme of my life then, what is $20 million going to do? Nothing. My life does not change. I live the same life regardless. I get what the union's saying. You don't want to go backward. Guys like Scherzer can push the market.”

Teams lined up to take their crack. On the first day of free agency, Epstein and the Cubs overnighted a DVD to Lester. The Kansas City Royals, one of the lowest-revenue teams in baseball, wanted in. Same with the Toronto Blue Jays and Detroit Tigers. The Atlanta Braves were Lester's secret dark horse, the team he
hoped would express more interest than it had in the early going. He and Farrah just bought their dream home in Atlanta's northern suburbs, near where the Braves were building their new stadium. Lester also could see himself wearing a New York Yankees jersey, the history of the franchise so rich.

He didn't know what to think about the Red Sox. They said they wanted him back. Carmine was wrong. So was Boston's ownership. Even though Lester understood why the Red Sox traded him to Oakland, it hurt him. And here they were, the unabashed and apologetic aggressors. They wanted the first official meeting, a request Lester granted. He would open the front doors of his home, and in would come the Red Sox trying to do what they'd screwed up once already.

“I'm sure there will be some awkward moments,” Lester said. “It's kind of like when you get divorced, you meet your ex-wife for the first time, and want to talk about everything and figure out where it went wrong.”

H
ERE'S WHERE IT WENT WRONG:
the Red Sox looked at the arm rationally in a marketplace without oxygen for rational thought. Logic dictated that no team should hand out five- or six- or seven-year deals to pitchers entering their decline phase. Logic's enemy happens to be scarcity, and so few pitchers like Jon Lester existed that even the Boston Red Sox, one of baseball's proudest franchises, resorted to groveling in hopes he would come back.

“I want to apologize that we're even here.” Those were the first words of the meeting on November 14, 2014, from Tom Werner, the Red Sox chairman, who was joined by principal owner John Henry, president Larry Lucchino, COO Sam Kennedy, and GM Ben Cherington—the five highest-ranking people in the Red Sox hierarchy.

Werner was a dealmaker, at home in a setting like this, a spacious living room with a group surrounding a table. He lived for
this. By the time he was thirty, the Harvard-educated Werner was running a TV production company that would launch
The Cosby Show
and make him hundreds of millions of dollars. He later bought the San Diego Padres, sold them after an embarrassing dismantling, slinked his way into Boston's new ownership triumvirate, and basked in three World Series titles since 2004. The success bolstered an ego already inflated; three months earlier, Werner had made an unsuccessful power grab, trying to wrest baseball's open commissioner job from the favorite and ultimate appointee, Rob Manfred. Now, Werner found himself in front of a far easier audience than thirty billionaires: Lester, Farrah, Seth Levinson, and two other ACES agents, Keith Miller and Josh Yates.

The Red Sox tried to leaven the conversation. “Listen, Jon,” Kennedy said, “if you sign back, I was talking to the CEO of Dunkin' Donuts. We'll get you free coffee for the rest of your life.” To which Miller replied: “Can the agent get free donuts for life then as well?”

When Cherington started to talk, Lester sat rapt. He was a worthy replacement for Epstein as GM, intelligent enough to navigate the political complexities of a team with an ownership Cerberus. Running the Red Sox's baseball-operations department was one giant booby trap. Autonomy was only as good as the whims of the owners. Cherington had bitten his tongue raw in 2012 as the ownership's handpicked manager, Bobby Valentine, self-immolated and torched the Red Sox's season. The initial offer to Lester had been another classic tone-deaf move.

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